56-91-7

Basic information

• Product Name: 4-(Aminomethyl)benzoic acid
• Synonyms: H-4-AMB-OH;H-(4)AMBZ-OH;LABOTEST-BB LT00053184;AMINOMETHYL BENZOIC ACID;4-CARBOXYBENZYLAMINE;4-(AMINOMETHYL)BENZOIC ACID;RARECHEM AL BW 0005;NH2-CH2-PH(4)-COOH
• CAS NO: 56-91-7
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• EINECS: 200-297-9
• Product Categories: Pharmaceutical Raw Materials;CARBOXYLICACID;Acids and Derivatives;Amines and Anilines;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Aromatic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 56-91-7.mol
• Article Data: 17

Chemical Properties

• Melting Point: ≥300 °C(lit.)
• Boiling Point: 273.17°C (rough estimate)
• Flash Point: 149.2 °C
• Appearance: White to almost white/Powder
• Density: 1.2023 (rough estimate)
• Refractive Index: 1.5810 (estimate)
• Storage Temp.: Store at 0-5°C
• Solubility: Aqueous Base (Slightly), Water (Slightly, Heated, Sonicated)
• PKA: 3.75±0.10(Predicted)
• Water Solubility: Slightly soluble in water. Insoluble in ethanol, benzene and chloroform.
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 1100606
• CAS DataBase Reference: 4-(Aminomethyl)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Aminomethyl)benzoic acid(56-91-7)
• EPA Substance Registry System: 4-(Aminomethyl)benzoic acid(56-91-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39-26,37/39
• WGK Germany: 3
• Hazardous Substances Data: 56-91-7(Hazardous Substances Data)

Usage

Description

4-(Aminomethyl)benzoic acid is a organic compound that can serve as a type 2 antifibrinolytic agent used in the treatment of fibrotic skin disorders, such as Peyronie's disease. It is believed that 4-(Aminomethyl)benzoic acid is effective to increase the oxygen uptake at the tissue level and enhance activity of monoamine oxidase, thus to promote the degradation of serotonin, which in excess, may lead to fibrotic changes. It is also administrated by mouth to treat several skin conditions including vitiligo, pemphigus, dermatomyositis, morphea, lymphoblastoma cutis and scleroderma. It is sometimes used in pill form by patients suffering from irritable bowel syndrome to treat the relevant gastrointestinal symptoms and applied in nutritional epidemiological studies to assess the completeness of 24-hour urine collection for the determination of urinary sodium, potassium, or nitrogen levels. Besides, it can also serve as nutritional supplements to darken gray hair, prevent hair loss, make skin look younger and prevent sunburn and its benefits are claimed for people with fatigue, irritability, depression, weeping eczema, scleroderma, patchy pigment loss in skin, and premature grey hair.

References

https://en.wikipedia.org/wiki/4-Aminobenzoic_acid https://www.alfa.com/en/catalog/B23519/ https://pubchem.ncbi.nlm.nih.gov/compound/4-aminobenzoic_acid#section=Top http://www.webmd.com/vitamins-supplements/ingredientmono-1004-PABA+PARA-AMINOBENZOIC+ACID+PABA.aspxactiveIngredientId=1004&activeIngredientName=PABA

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 56-91-7 differently. You can refer to the following data:
1. 4-(Aminomethyl)benzoic Acid is a type 2 antifibrinolytic agent.
2. 4-(Aminomethyl)benzoic acid acts as an unnatural amino acid derivative. It is also used as a type 2 antifibrinolytic agent. Further, it reacts with 2-methyl-isothiourea sulfate to prepare 4-guanidinomethylbenzoic acid.
3. 4-(Aminomethyl)benzoic acid (PAMBA) can be used in the synthesis of:Cobalt carboxy phosphonates.Apoptozole (Az), which has cellular potency to promote membrane trafficking of mutant cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel activity.Cyclopeptide composed of L-glutamic acid and 3-aminobenzoic acid that can be used as receptors for a variety of cations and anions.A bioactive peptide which has potent GPR54 (a G protein-coupled receptor) agonistic activity.

Synthetic route

p-Toluic acid (99-94-5) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
With ammonium peroxydisulfate; 2,2'-azobis-(2,4-dimethylvaleronitrile); hydrogen bromide In tetrachloromethane at 45℃; for 15h; Solvent; Reagent/catalyst; Temperature;	98%
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / 80 °C 2: triethylamine; potassium carbonate / tetrachloromethane / 4 h / 25 °C View Scheme

4-(hydroxyiminomethyl)benzoic acid methyl ester (53148-13-3) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
Stage #1: 4-(hydroxyiminomethyl)benzoic acid methyl ester With water; hydrogen; sodium hydroxide; 5%-palladium/activated carbon at 20℃; under 7355.72 Torr; for 3.5h; Stage #2: With hydrogenchloride In water pH=7;	95.8%
With water; hydrogen; sodium hydroxide; 5%-palladium/activated carbon at 20℃; under 7355.72 Torr; for 3.5h; Conversion of starting material;

4-bromomethylbenzoic Acid (6232-88-8) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
With potassium carbonate; triethylamine In tetrachloromethane at 25℃; for 4h; Temperature;	95.32%
With ammonium hydroxide

ethyl 4-(aminomethyl)benzoate (366-84-7) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
With sulfuric acid at 80℃; for 1h; Temperature;	91%
With sulfuric acid at 80℃; for 1h;	78.35%

methyl 4-(aminomethyl)benzoate (18469-52-8) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
With sulfuric acid at 50℃; for 1.5h;	87%
With sodium hydroxide; water

4-cyanobenzoic Acid (619-65-8) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
With hydrogen; Raney Nickel In methanol for 16h;	84%
With ammonium hydroxide; nickel Hydrogenation;
In ethanol

4-cyanobenzoic acid methyl ester (1129-35-7) → p-aminomethylbenzoic acid (56-91-7) + methyl 4-(aminomethyl)benzoate (18469-52-8) + methyl 4-((4-(aminomethyl)benzamido)methyl)benzoate

Conditions	Yield
With ammonia; nickel	A 21.9% B 44.3% C 6.2%

p-carboxybenzaldehyde oxime (3477-93-8) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
With palladium on activated charcoal; ethanol Hydrogenation;

4-[(2-carboxy-benzoylamino)-methyl]-benzoic acid (303795-50-8) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
With hydrogenchloride at 200℃; im Druckrohr;

hexamethylenetetramine (100-97-0) + 4-iodomethyl-benzoic acid ethyl ester → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
With hydrogenchloride; chloroform

hydrogenchloride (7647-01-0) + 4-[(2-carboxy-benzoylamino)-methyl]-benzoic acid (303795-50-8) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
at 200℃;

4-Carboxybenzaldehyde (619-66-9) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
Stage #1: 4-Carboxybenzaldehyde With Rink resin; trimethyl orthoformate at 25℃; for 2h; Stage #2: With lithium borohydride In tetrahydrofuran at 65℃; for 5h; Stage #3: With trifluoroacetic acid In dichloromethane at 25℃;

4-amino-benzoic acid (150-13-0) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH solution; nickel (II)-sulfate; water / Diazotization.weiteres Reagens: wss. Salzsaeure; anschliessendes Erwaermen 2: Raney nickel; aqueous ammonia / Hydrogenation View Scheme

4-cyanobenzyl bromide (17201-43-3) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous hydrochloric acid 2: aqueous ammonia View Scheme

4-aminobenzyl cyanide (10406-25-4) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
With sodium hydroxide; sulfuric acid

methyl 4-formylbenzoate (1571-08-0) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydroxylamine hydrochloride / water; methanol / 2 h / 25 - 35 °C 1.2: pH 7.5 - 8 2.1: hydrogen; sodium hydroxide; water / 5%-palladium/activated carbon / 3.5 h / 20 °C / 7355.72 Torr 2.2: pH 7 View Scheme
Multi-step reaction with 2 steps 1.1: hydroxylamine hydrochloride / 5%-palladium/activated carbon / water; methanol / 2 h / 25 - 35 °C 1.2: pH 7.5 - 8 2.1: hydrogen; sodium hydroxide; water / 5%-palladium/activated carbon / 3.5 h / 20 °C / 7355.72 Torr View Scheme

4-(hydroxyiminomethyl)benzoic acid methyl ester (53148-13-3) → p-aminomethylbenzoic acid (56-91-7) + p-carboxybenzaldehyde oxime (3477-93-8)

Conditions	Yield
With hydrogen; sodium hydroxide; 5%-palladium/activated carbon In water at 20℃; under 7355.72 Torr; for 8.5h; Conversion of starting material;

(S)-1-phenyl-ethylamine (2627-86-3) + 4-Carboxybenzaldehyde (619-66-9) → p-aminomethylbenzoic acid (56-91-7) + acetophenone (98-86-2)

Conditions	Yield
With pyridoxal 5'-phosphate; recombinant ω-transaminase from Burkholderia vietnamiensis G4 In aq. phosphate buffer at 37℃; for 0.0833333h; pH=7.4; Enzymatic reaction;

monomethyl monopotassium terephthalate (42967-55-5) → p-aminomethylbenzoic acid (56-91-7) + methyl 4-(aminomethyl)benzoate (18469-52-8) + methyl 4-((4-(aminomethyl)benzamido)methyl)benzoate

Conditions	Yield
Multi-step reaction with 4 steps 1: bis(trichloromethyl) carbonate / toluene; N,N-dimethyl-formamide / Reflux 2: ammonia / water / 1.5 h / 0 - 20 °C 3: acetic anhydride / Reflux 4: ammonia; nickel View Scheme

1,4-benzenedicarboxylic acid dimethyl ester (120-61-6) → p-aminomethylbenzoic acid (56-91-7) + methyl 4-(aminomethyl)benzoate (18469-52-8) + methyl 4-((4-(aminomethyl)benzamido)methyl)benzoate

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium hydroxide / methanol / 45 - 50 °C 2: bis(trichloromethyl) carbonate / toluene; N,N-dimethyl-formamide / Reflux 3: ammonia / water / 1.5 h / 0 - 20 °C 4: acetic anhydride / Reflux 5: ammonia; nickel View Scheme
Multi-step reaction with 5 steps 1: potassium hydroxide / methanol; toluene / 5.5 h / 45 - 50 °C 2: bis(trichloromethyl) carbonate / toluene; N,N-dimethyl-formamide / Reflux 3: ammonia / water / 1.5 h / 0 - 20 °C 4: acetic anhydride / Reflux 5: ammonia; nickel View Scheme

4-Methoxycarbonylbenzoyl chloride (7377-26-6) → p-aminomethylbenzoic acid (56-91-7) + methyl 4-(aminomethyl)benzoate (18469-52-8) + methyl 4-((4-(aminomethyl)benzamido)methyl)benzoate

Conditions	Yield
Multi-step reaction with 3 steps 1: ammonia / water / 1.5 h / 0 - 20 °C 2: acetic anhydride / Reflux 3: ammonia; nickel View Scheme

methyl-4-carbamoylbenzoate (6757-31-9) → p-aminomethylbenzoic acid (56-91-7) + methyl 4-(aminomethyl)benzoate (18469-52-8) + methyl 4-((4-(aminomethyl)benzamido)methyl)benzoate

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic anhydride / Reflux 2: ammonia; nickel View Scheme

p-methyloxycarbonylbenzyl chloride (34040-64-7) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; 5-methyl-1,3,4-thiadiazol-2-amine / ethanol; water / 0.5 h / 100 °C 2: sulfuric acid / 1.5 h / 50 °C View Scheme

ethyl 4-chloromethylbenzoate (1201-90-7) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; 5-methyl-1,3,4-thiadiazol-2-amine / ethanol; water / 1.5 h / 80 °C 2: sulfuric acid / 1 h / 80 °C View Scheme

phthalic anhydride (85-44-9) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: water; sodium hydroxide / 3 h / 80 - 150 °C 2: ammonium hydroxide / 1 h / 180 °C 3: aluminum (III) chloride / diethyl ether / 1 h / 40 °C 4: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / 80 °C 5: triethylamine; potassium carbonate / tetrachloromethane / 4 h / 25 °C View Scheme

benzoic acid (65-85-0) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: aluminum (III) chloride / diethyl ether / 1 h / 40 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / 80 °C 3: triethylamine; potassium carbonate / tetrachloromethane / 4 h / 25 °C View Scheme

benzene-1,2-dicarboxylic acid (88-99-3) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: ammonium hydroxide / 1 h / 180 °C 2: aluminum (III) chloride / diethyl ether / 1 h / 40 °C 3: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / 80 °C 4: triethylamine; potassium carbonate / tetrachloromethane / 4 h / 25 °C View Scheme

p-(chloromethyl)benzoic acid (1642-81-5) → p-aminomethylbenzoic acid (56-91-7)

Conditions	Yield
Stage #1: p-(chloromethyl)benzoic acid With hexamethylenetetramine In methanol; water for 1h; Stage #2: With ammonia In methanol; water at 50 - 60℃;

methanol (67-56-1) + p-aminomethylbenzoic acid (56-91-7) → methyl 4-(aminomethyl)benzoate hydrochloride (6232-11-7)

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 24h;	100%
With thionyl chloride at 20℃; for 96h;	99%
With thionyl chloride at 0℃; for 24h; Reflux;	99%

p-aminomethylbenzoic acid (56-91-7) + lactobionolactone (5965-65-1, 42776-28-3, 52762-22-8) → lactoseamidemethylbenzoic acid (173543-54-9)

Conditions	Yield
In dimethyl sulfoxide at 130 - 150℃; for 3h;	100%

p-aminomethylbenzoic acid (56-91-7) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → N-(9-fluorenylmethyloxycarbonyl)-4-(aminomethyl)benzoic acid (164470-64-8)

Conditions	Yield
With sodium carbonate In 1,4-dioxane; water	100%
With sodium carbonate In 1,4-dioxane; water at 20℃; for 12h;	90%
With sodium hydrogencarbonate In 1,4-dioxane at 0℃; for 3h;	68.1%

p-aminomethylbenzoic acid (56-91-7) + acrylic acid methyl ester (292638-85-8) → 4-{[bis-(2-methoxycarbonyl-ethyl)-amino]-methyl}-benzoic acid

Conditions	Yield
In methanol at 20℃; for 12h;	100%

p-aminomethylbenzoic acid (56-91-7) + isobutyryl chloride (79-30-1) → 4-[(isobutyrylamino)methyl]benzoic acid (908495-37-4)

Conditions	Yield
Stage #1: p-aminomethylbenzoic acid; isobutyryl chloride With triethylamine In dichloromethane for 132h; Stage #2: With hydrogenchloride In dichloromethane; water; ethyl acetate pH=1;	100%

p-aminomethylbenzoic acid (56-91-7) + isatoic anhydride (118-48-9) → 4-((2-aminobenzamido)methyl)benzoic acid (503039-57-4)

Conditions	Yield
With triethylamine In water at 40℃; for 3h;	100%
With triethylamine In water	72%
With triethylamine In water	72%
With dmap; triethylamine In pyridine; N,N-dimethyl-formamide at 80℃; for 16h;	70.7%
In water at 20℃; for 2h; Green chemistry;

p-aminomethylbenzoic acid (56-91-7) + ethanol (64-17-5) → p-(Aminometyl)benzoic acid ethyl ester hydrochloride (6232-12-8)

Conditions	Yield
With hydrogenchloride In water Reflux;	100%
With thionyl chloride at 0℃; for 3h; Heating / reflux;

p-aminomethylbenzoic acid (56-91-7) + phenyl isothiocyanate (103-72-0) → 4-[(3-phenyl-tioureido)methyl]benzoic acid (356773-26-7)

Conditions	Yield
In ethanol for 24h; Reflux;	100%
In ethanol Reflux;

p-aminomethylbenzoic acid (56-91-7) + tri-tert-butyl 2,2',2''-(10-(2-((2,5-dioxopyrrolidin-1-yl)oxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate (819869-77-7) → C36H59N5O9

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;	100%

p-aminomethylbenzoic acid (56-91-7) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → N-(9-fluorenylmethyloxycarbonyl)-4-(aminomethyl)benzoic acid (164470-64-8)

Conditions	Yield
With sodium carbonate In 1,4-dioxane at 40℃; for 12h;	99%
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 3.8h;	93.5%
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 2h; Acylation;	77.7%

p-aminomethylbenzoic acid (56-91-7) + 3-Bromobenzenesulfonyl chloride (2905-24-0) → 4-{[(3-bromophenyl)sulfonamido]methyl}benzoic acid

Conditions	Yield
With Sodium borate In water at 20℃; for 16.0833h; Sonication;	99%

p-aminomethylbenzoic acid (56-91-7) → methyl 4-(aminomethyl)benzoate hydrochloride (6232-11-7)

Conditions	Yield
With methanol; thionyl chloride Reflux;	98.3%
With thionyl chloride In methanol at 20℃; for 16h;	97%
With hydrogenchloride In methanol

p-aminomethylbenzoic acid (56-91-7) + di-tert-butyl dicarbonate (24424-99-5) → 4-(tert-Butoxycarbonylaminomethyl)benzoic acid (33233-67-9)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane at 0 - 20℃; for 24h;	98%
Stage #1: p-aminomethylbenzoic acid; di-tert-butyl dicarbonate With sodium hydrogencarbonate In tetrahydrofuran; water for 16h; pH=~ 6; Stage #2: With hydrogenchloride; water In tetrahydrofuran pH=~ 3;	97%
Stage #1: p-aminomethylbenzoic acid; di-tert-butyl dicarbonate With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 16h; pH=6; Stage #2: With hydrogenchloride; water In water pH=3;	97%

3-hydroxymethylpyridin (100-55-0) + p-aminomethylbenzoic acid (56-91-7) → 4-benzoic acid (241809-79-0)

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium chloride; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide	98%
Stage #1: 3-hydroxymethylpyridin With 1,1'-carbonyldiimidazole In tetrahydrofuran at 10 - 20℃; for 1h; Stage #2: p-aminomethylbenzoic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In tetrahydrofuran at 20℃; for 5h; Stage #3: With hydrogenchloride; water pH=5;	91%

p-aminomethylbenzoic acid (56-91-7) + 4-fluoro-3-chlorobenzenesulfonyl chloride (91170-93-3) → 4-{[(3-chloro-4-fluorophenyl)sulfonamido]methyl}benzoic acid (690646-06-1)

Conditions	Yield
With borax In water at 20℃; for 4h; Sonication;	98%
With Sodium borate In water at 20℃; for 4.08333h; Sonication;	98%

p-aminomethylbenzoic acid (56-91-7) → 4-hydroxymethyl-benzylamine (39895-56-2)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux;	97%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 12h; Reflux;	97%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Inert atmosphere; Reflux;	65%

p-aminomethylbenzoic acid (56-91-7) + benzyl chloroformate (501-53-1) → 4-((benzyloxycarbonylamino)methyl)benzoic acid (58933-52-1)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 16h;	97%
In water at 20℃; for 16h;	95%
In water at 0 - 20℃;	95%

p-aminomethylbenzoic acid (56-91-7) + trifluoroacetic anhydride (407-25-0) → 4-[[(2,2,2-trifluoroacetyl)amino]methyl]benzoic acid (130029-61-7)

Conditions	Yield
at 0 - 20℃; for 2h;	97%
for 2h;	93%
at 25℃; for 2h;	88%

p-aminomethylbenzoic acid (56-91-7) + 9-Chloroacridine (1207-69-8) → 4-((acridin-9-amino)methyl)benzoic acid (1211776-25-8)

Conditions	Yield
In 2-ethoxy-ethanol at 90 - 100℃;	97%

p-aminomethylbenzoic acid (56-91-7) + phenyl isocyanate (103-71-9) → 4-<<<(phenylamino)carbonyl>amino>methyl>benzoic acid

Conditions	Yield
With sodium hydroxide at 23℃; for 1h;	96%

p-aminomethylbenzoic acid (56-91-7) + benzene-1,2-dicarboxylic acid (88-99-3) → 4-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]benzoic acid (227598-41-6)

Conditions	Yield
In acetonitrile at 180℃; for 0.5h; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube; Microwave irradiation;	96%

p-aminomethylbenzoic acid (56-91-7) + 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-ethoxycyclobut-3-ene-1,2-dione (1233032-09-1) → 3,5-bis[trifluoromethyl]phenyl squaramide-4-aminomethyl benzoic acid

Conditions	Yield
With sodium carbonate In ethanol at 135℃; for 0.583333h; Microwave irradiation; Sealed tube;	96%

3-Sulfolene (77-79-2) + p-aminomethylbenzoic acid (56-91-7) → 4-(N-(3-tetrahydrothiophenyl-1,1-dioxide)aminomethyl)benzoic acid

Conditions	Yield
With potassium hydroxide In water at 55℃; for 23h;	95%

methanol (67-56-1) + p-aminomethylbenzoic acid (56-91-7) → methyl 4-(aminomethyl)benzoate (18469-52-8)

Conditions	Yield
With hydrogenchloride In water at 85℃; for 16h; Fischer–Speier Esterification;	95%
With thionyl chloride for 6h; Heating / reflux;	92%
With sulfuric acid for 6h; Reflux;	92%

p-aminomethylbenzoic acid (56-91-7) + N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (152120-54-2, 862686-58-6, 1143572-00-2) → N,N'-bis-tert-butoxycarbonyl-4-guanidinomethyl-benzoic acid (246224-53-3)

Conditions	Yield
With triethylamine In tetrahydrofuran Heating;	95%

morpholine (110-91-8) + p-aminomethylbenzoic acid (56-91-7) + 4-fluorophthalic anhydride (319-03-9) → 4-{[5-(morpholin-4-yl)-1,3-dioxoisoindol-2-yl]methyl}benzoic acid (1613391-57-3)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 200℃; for 1.25h; Inert atmosphere; Microwave irradiation;	95%

p-aminomethylbenzoic acid (56-91-7) + 4-fluorophenyl isothiocyanate (1544-68-9) → 4-{[3-(4-fluorophenyl)thioureido]methyl}benzoic acid

Conditions	Yield
In ethanol for 24h; Reflux;	95%

Upstream product

• 10406-25-4 4-aminobenzyl cyanide 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 619-66-9 4-Carboxybenzaldehyde 
• 1642-81-5 p-(chloromethyl)benzoic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 65-85-0 benzoic acid 
• 85-44-9 phthalic anhydride 
• 99-94-5 p-Toluic acid 
• 366-84-7 ethyl 4-(aminomethyl)benzoate 
• 1201-90-7 ethyl 4-chloromethylbenzoate 
• 34040-64-7 p-methyloxycarbonylbenzyl chloride 
• 1129-35-7 4-cyanobenzoic acid methyl ester 
• 6757-31-9 methyl-4-carbamoylbenzoate 
• 7377-26-6 4-Methoxycarbonylbenzoyl chloride 

Downstream Products

• 366-84-7 ethyl 4-(aminomethyl)benzoate 
• 41931-42-4 4,4'-(2-thioxo-[1,3,5]thiadiazinane-3,5-diyldimethyl)-bis-benzoic acid 
• 3477-93-8 p-carboxybenzaldehyde oxime 
• 41987-12-6 4-(5-benzyl-6-thioxo-[1,3,5]thiadiazinan-3-ylmethyl)-benzoic acid 
• 41931-43-5 4-[5-(5-carboxy-pentyl)-6-thioxo-[1,3,5]thiadiazinan-3-ylmethyl]-benzoic acid 
• 137094-03-2 C₂₆H₁₉NO₄ 
• 76064-18-1 C₁₇H₃₃NO₂Si₃ 
• 135672-66-1 4- benzoic acid 
• 6232-11-7 methyl 4-(aminomethyl)benzoate hydrochloride 
• 173543-54-9 lactoseamidemethylbenzoic acid 
• 194039-59-3 2,4-diamino-5-{4'-[N-(4''-carboxybenzyl)amino]-3'-nitrophenyl}-6-ethylpyrimidine 
• 164470-64-8 N-(9-fluorenylmethyloxycarbonyl)-4-(aminomethyl)benzoic acid 
• 176908-49-9 C₂₅H₂₃N₃O₆ 
• 212776-97-1 4-(8-methoxycarbonyloxy-2,4-dioxo-1,3-benzoxazin-3-yl-methyl)-benzoic acid 

Relevant articles and documents

Novel preparation method of aminomethylbenzoic acid

The invention belongs to the technical field of medicines, and relates to a novel preparation method of aminomethylbenzoic acid, acetamide is adopted as a novel nitrogen source for synthesis of aminomethylbenzoic acid, the preparation method is green, environment-friendly, cheap, easy to obtain and high in safety, and specifically, ethyl p-chloromethyl benzoate is subjected to acetamide amination to obtain p-acetamidomethyl benzamide, and then hydrolysis and neutralization reactions are carried out to obtain aminomethylbenzoic acid.

Preparation method of aminomethylbenzoic acid

The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of aminomethylbenzoic acid. The method comprises the following steps: carrying outchlorination reaction on p-toluic acid and a chlorination reagent under the condition of a catalyst I to obtain an intermediate p-chloromethylbenzoic acid, and carrying out ammonolysis on the intermediate p-chloromethylbenzoic acid and ammonia water under the condition of a catalyst II to prepare aminomethylbenzoic acid. The purity of the obtained product aminomethylbenzoic acid is greater than 99.9%, the single impurity content is less than 0.1%, and the overall yield of the two-step reaction is greater than 63%. The method is short in synthetic route, free of highly toxic reagents or precious metals, low in production cost, less in environmental pollution, high in overall yield and suitable for large-scale industrial production.

Synthetic method for aminomethylbenzoic acid

The invention discloses a synthetic method for aminomethylbenzoic acid. The synthetic method specifically comprises the following steps: adding 4-halomethyl alkyl benzoate and triethylamine, dropwiseadding ethanol-water solution in which 2-amino-5-methyl-1,3,4-thiadiazole is dissolved while stirring, after a reaction is completed, evaporating solution until a lot of solids are separated out, cooling, filtering, and drying to obtain 4-aminomethyl alkyl benzoate; adding the 4-aminomethyl alkyl benzoate to acid solution, reacting by stirring, cooling, adding water, and dropwise adding alkali until the solution is alkaline, and a lot of the solids are separated out, filtering, washing, and drying to obtain the aminomethylbenzoic acid. The synthetic method is moderate in reaction conditions, less in side reactions, high in yield, low in cost, short in reaction and post-processing time, low in energy consumption, high in production efficiency, small in environmental pollution, and simple in'three wastes' treatment, and suitable for the industrial production. -CN with strong toxicity and an organic solvent with strong pollution are not used, and reaction raw materials are cheap in priceand easy to obtain.