2100-31-4

Basic information

• Product Name: 2-Propoxybenzoic acid
• Synonyms: RARECHEM AL BO 0876;O-PROPOXY BENZOIC ACID;AKOS BBB/270;2-PROPOXYBENZOIC ACID;2-N-PROPOXYBENZOIC ACID;2-n-Propoxybenzoic acid, 98+%;2-Propoxybenzoic aci;Salicylic Acid Propyl Ether
• CAS NO: 2100-31-4
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2
• EINECS: 603-128-0
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids;Acids & Esters;Anisoles, Alkyloxy Compounds & Phenylacetates
• Mol File: 2100-31-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 35-37°C
• Boiling Point: 207 °C / 40mmHg
• Flash Point: 120 °C
• Appearance: /
• Density: 1.133 g/cm³
• Vapor Pressure: 0.00034mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: DMSO, Methanol
• PKA: pK1:4.24 (20°C)
• BRN: 3089998
• CAS DataBase Reference: 2-Propoxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propoxybenzoic acid(2100-31-4)
• EPA Substance Registry System: 2-Propoxybenzoic acid(2100-31-4)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37
• RTECS: 000-000-0
• Hazardous Substances Data: 2100-31-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 2100-31-4 differently. You can refer to the following data:
1. 2-Propoxybenzoic Acid is a salicylic acid derivative used in the preparation of inhibitors of tyrosinase or hyaluronidase. 2-Propoxybenzoic Acid is a very potent inhibitior of collagen-induced aggrega tion of human platelets
2. 2-Propoxybenzoic Acid is a salicylic acid derivative used in the preparation of inhibitors of tyrosinase or hyaluronidase. 2-Propoxybenzoic Acid is a very potent inhibitior of collagen-induced aggregation of human platelets

InChI:InChI=1/C10H12O3/c1-2-7-13-9-6-4-3-5-8(9)10(11)12/h3-6H,2,7H2,1H3,(H,11,12)/p-1

Synthetic route

2-propoxybenzoic acid propyl ester (92156-43-9) → 2-propoxybenzoic acid (2100-31-4)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at 0 - 30℃;	95%
Stage #1: 2-propoxybenzoic acid propyl ester With potassium tert-butylate In dimethyl sulfoxide at 70℃; for 2h; Stage #2: With hydrogenchloride; water In dimethyl sulfoxide at 0 - 10℃;	80%

2-allyloxybenzoic acid (59086-52-1) → 2-propoxybenzoic acid (2100-31-4)

Conditions	Yield
Stage #1: 2-allyloxybenzoic acid With sodium hydroxide In water for 0.25h; Stage #2: With sodium tetrahydroborate In water at 20 - 60℃;	90%

methyl-2-propoxybenzoic acid (18167-33-4) → 2-propoxybenzoic acid (2100-31-4)

Conditions	Yield
With sodium hydroxide
With sodium hydroxide
With sodium hydroxide In methanol for 2h; Heating; Yield given;

2-propoxy-benzoic acid ethyl ester (856306-04-2) → 2-propoxybenzoic acid (2100-31-4)

Conditions	Yield
With sodium hydroxide
With sodium hydroxide

1-iodo-propane (107-08-4) + salicylic acid (69-72-7) → 2-propoxybenzoic acid (2100-31-4)

Conditions	Yield
With propan-1-ol; potassium hydroxide im Druckrohr;

methyl salicylate (119-36-8) + aqueous methanol. LiOH → 2-propoxybenzoic acid (2100-31-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3, KI / acetone / 48 h / Heating 2: NaOH / methanol / 2 h / Heating View Scheme

2-hydroxy-benzoic acid ethyl ester (118-61-6) → 2-propoxybenzoic acid (2100-31-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium ethylate 2: ethanolic NaOH-solution View Scheme

salicylic acid (69-72-7) → 2-propoxybenzoic acid (2100-31-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 70 - 80 °C 2: potassium tert-butylate / dimethyl sulfoxide / 0 - 30 °C View Scheme

tert.-butylhydroperoxide (75-91-2) + 2-propoxybenzoic acid (2100-31-4) → methyl-2-propoxybenzoic acid (18167-33-4)

Conditions	Yield
Stage #1: tert.-butylhydroperoxide; 2-propoxybenzoic acid In water; dimethyl sulfoxide Stage #2: In water; dimethyl sulfoxide at 100℃; for 20h; Sealed tube;	96%

2-propoxybenzoic acid (2100-31-4) + 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide (139756-02-8) → 1-Methyl-4-(2-n-propoxybenzamido)-3-n-propylpyrazole-5-carboxamide (139756-04-0)

Conditions	Yield
Stage #1: 2-propoxybenzoic acid With thionyl chloride In dichloromethane for 3h; Heating / reflux; Stage #2: 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide With dmap; triethylamine In dichloromethane at 0℃; for 1h;	92%
With 2-(Dimethylamino)pyridine; thionyl chloride; triethylamine In dichloromethane

d3-4-amino-2-methyl-5-propyl-2H-pyrazole-3-carboxylic acid amide (526203-31-6) + 2-propoxybenzoic acid (2100-31-4) → d3-2-methyl-4-(2-propoxybenzoylamino)-5-propyl-2H-pyrazole-3-carboxylic acid amide (1046784-62-6)

Conditions	Yield
Stage #1: 2-propoxybenzoic acid With thionyl chloride In dichloromethane for 3h; Heating / reflux; Stage #2: d3-4-amino-2-methyl-5-propyl-2H-pyrazole-3-carboxylic acid amide With dmap; triethylamine In dichloromethane at 0℃; for 1h; Product distribution / selectivity;	91%

2-propoxybenzoic acid (2100-31-4) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methoxy-N-methyl-2-propoxybenzamide

Conditions	Yield
Stage #1: 2-propoxybenzoic acid With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In tetrahydrofuran; ethyl acetate at 0 - 5℃; for 0.166667h; Inert atmosphere; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In tetrahydrofuran; ethyl acetate at 0 - 25℃; for 1.83333h; Inert atmosphere;	90%

2-propoxybenzoic acid (2100-31-4) + 1,1-dimethylhydrazine (57-14-7) → N',N'-dimethyl-2-propoxybenzohydrazide (1094024-18-6)

Conditions	Yield
Stage #1: 2-propoxybenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In 1,2-dichloro-ethane at 20℃; for 3h; Stage #2: N,N-Dimethylhydrazine With 4-methyl-morpholine In 1,2-dichloro-ethane at 20℃; for 20h; Cooling with ice;	87%

2-((S)-2-Amino-1-hydroxy-hexyl)-thiazole-4-carboxylic acid ethyl ester (865537-45-7) + 2-propoxybenzoic acid (2100-31-4) → 2-[(S)-1-Hydroxy-2-(2-propoxy-benzoylamino)-hexyl]-thiazole-4-carboxylic acid ethyl ester

Conditions	Yield
With hydrogenchloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 4-methyl-morpholine In 1,4-dioxane	86%

2-(phenylthio)ethanamine (2014-75-7) + 2-propoxybenzoic acid (2100-31-4) → N-(2-(phenylthio)ethyl)-2-propoxybenzamide

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	85%

2-propoxybenzoic acid (2100-31-4) → 5-Chlorosulphonyl-2-n-propoxybenzoic Acid (215299-78-8)

Conditions	Yield
With chlorosulfonic acid; sodium hydroxide; thionyl chloride In dichloromethane; water at -10 - 20℃; for 1.83333h;	80%
With chlorosulfonic acid at -5 - 25℃;	1.2 g
With chlorosulfonic acid; thionyl chloride In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran

3-amino-1-methyl-4-propyl-1H-pyrrole-2-carboxamide (356044-93-4) + 2-propoxybenzoic acid (2100-31-4) → 1-methyl-3-(2-propoxybenzamido)-4-propyl-1H-pyrrole-2-carboxamide (356044-98-9)

Conditions	Yield
Stage #1: 2-propoxybenzoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 15℃; for 0.5h; Stage #2: 3-amino-1-methyl-4-propyl-1H-pyrrole-2-carboxamide In N,N-dimethyl-formamide at 20℃; for 1.58333h;	76%

2,3-Diaminopyridine (452-58-4) + 2-propoxybenzoic acid (2100-31-4) → 2-(2-propoxyphenyl)-1H-imidazo<4,5-b>pyridine

Conditions	Yield
With trichlorophosphate for 7h; Heating;	69%

2-propoxybenzoic acid (2100-31-4) + 3-amino-5-phenyl-1,3-dihydrobenzo[e][1,4]diazepin-2-one (103343-47-1) → N-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-2-propoxy-benzamide

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;	58%

2-propoxybenzoic acid (2100-31-4) + adenine (66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9) → N6-[2-(n-propoxy)benzoyl]adenine

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100 - 130℃; Inert atmosphere;	20%

3-hydrazino-5-methyl-1,2,4-triazino[5,6-b]indole (3993-27-9) + 2-propoxybenzoic acid (2100-31-4) → 2-propoxy-benzoic acid N'-(5-methyl-5H-1,2,4-triazino[5,6-b]indol-3-yl)-hydrazide (729594-53-0)

Conditions	Yield
Stage #1: 2-propoxybenzoic acid With Carbonyldiimidazole In DMF (N,N-dimethyl-formamide) at 80℃; for 0.166667h; Stage #2: 3-hydrazino-5-methyl-1,2,4-triazino[5,6-b]indole In DMF (N,N-dimethyl-formamide) at 40 - 80℃; for 0.166667h;	19%

2-propoxybenzoic acid (2100-31-4) → 2-propoxybenzoyl chloride (54090-36-7)

Conditions	Yield
With phosphorus pentachloride
With thionyl chloride; N,N-dimethyl-formamide In hexane for 1h; Heating / reflux;
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide for 2h; Cooling with ice; Reflux;
With thionyl chloride In dichloromethane at 100℃; for 0.5h; Cooling with ice;

2-propoxybenzoic acid (2100-31-4) → 5-nitro-2-propoxybenzoic acid (13736-91-9)

Conditions	Yield
With nitric acid; Nitrogen dioxide In acetic acid

2-propoxybenzoic acid (2100-31-4) + 5,6-diamino-1-isobutyl-3-methyl-1H-pyrimidine-2,4-dione (78033-18-8) → 3-isobutyl-1-methyl-8-(2-propoxy-phenyl)-3,7-dihydro-purine-2,6-dione (503809-60-7)

Conditions	Yield
Stage #1: 2-propoxybenzoic acid; 5,6-diamino-1-isobutyl-3-methyl-1H-pyrimidine-2,4-dione With benzotriazol-1-ol In dichloromethane at 40℃; Stage #2: With sodium hydroxide In methanol at 60℃;

2-propoxybenzoic acid (2100-31-4) → 3-(3-isobutyl-1-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-4-propoxy-benzenesulfonyl chloride

Conditions	Yield
Multi-step reaction with 2 steps 1.1: WSCD; aq. HOBt / CH2Cl2 / 40 °C 1.2: aq. NaOH / methanol / 60 °C 2.1: ClSO3H / 0.5 h / 40 - 60 °C View Scheme

2-propoxybenzoic acid (2100-31-4) → 3-(3-isobutyl-1-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-4-propoxy-benzenesulfonamide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: WSCD; aq. HOBt / CH2Cl2 / 40 °C 1.2: aq. NaOH / methanol / 60 °C 2.1: ClSO3H / 0.5 h / 40 - 60 °C 3.1: NH3 / dimethylformamide / 18 h / 20 °C View Scheme

2-propoxybenzoic acid (2100-31-4) → N-(2-dimethylamino-ethyl)-3-(3-isobutyl-1-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-N-methyl-4-propoxy-benzenesulfonamide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: WSCD; aq. HOBt / CH2Cl2 / 40 °C 1.2: aq. NaOH / methanol / 60 °C 2.1: ClSO3H / 0.5 h / 40 - 60 °C 3.1: dimethylformamide / 18 h / 20 °C View Scheme

2-propoxybenzoic acid (2100-31-4) → N-(2-dimethylamino-ethyl)-N-ethyl-3-(3-isobutyl-1-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-4-propoxy-benzenesulfonamide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: WSCD; aq. HOBt / CH2Cl2 / 40 °C 1.2: aq. NaOH / methanol / 60 °C 2.1: ClSO3H / 0.5 h / 40 - 60 °C 3.1: dimethylformamide / 18 h / 20 °C View Scheme

2-propoxybenzoic acid (2100-31-4) → 3-isobutyl-1-methyl-8-[5-(4-methyl-piperazine-1-sulfonyl)-2-propoxy-phenyl]-3,7-dihydro-purine-2,6-dione

Conditions	Yield
Multi-step reaction with 3 steps 1.1: WSCD; aq. HOBt / CH2Cl2 / 40 °C 1.2: aq. NaOH / methanol / 60 °C 2.1: ClSO3H / 0.5 h / 40 - 60 °C 3.1: dimethylformamide / 18 h / 20 °C View Scheme

2-propoxybenzoic acid (2100-31-4) → 8-[5-(4-ethyl-piperazine-1-sulfonyl)-2-propoxy-phenyl]-3-isobutyl-1-methyl-3,7-dihydro-purine-2,6-dione

Conditions	Yield
Multi-step reaction with 3 steps 1.1: WSCD; aq. HOBt / CH2Cl2 / 40 °C 1.2: aq. NaOH / methanol / 60 °C 2.1: ClSO3H / 0.5 h / 40 - 60 °C 3.1: dimethylformamide / 18 h / 20 °C View Scheme

2-propoxybenzoic acid (2100-31-4) → 8-{5-[4-(2-hydroxy-ethyl)-piperidine-1-sulfonyl]-2-propoxy-phenyl}-3-isobutyl-1-methyl-3,7-dihydro-purine-2,6-dione

Conditions	Yield
Multi-step reaction with 3 steps 1.1: WSCD; aq. HOBt / CH2Cl2 / 40 °C 1.2: aq. NaOH / methanol / 60 °C 2.1: ClSO3H / 0.5 h / 40 - 60 °C 3.1: dimethylformamide / 18 h / 20 °C View Scheme

2-propoxybenzoic acid (2100-31-4) → 8-{5-[4-(2-hydroxy-ethyl)-piperazine-1-sulfonyl]-2-propoxy-phenyl}-3-isobutyl-1-methyl-3,7-dihydro-purine-2,6-dione

Conditions	Yield
Multi-step reaction with 3 steps 1.1: WSCD; aq. HOBt / CH2Cl2 / 40 °C 1.2: aq. NaOH / methanol / 60 °C 2.1: ClSO3H / 0.5 h / 40 - 60 °C 3.1: dimethylformamide / 18 h / 20 °C View Scheme

Upstream product

• 107-08-4 1-iodo-propane 
• 69-72-7 salicylic acid 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 59086-52-1 2-allyloxybenzoic acid 
• 92156-43-9 2-propoxybenzoic acid propyl ester 
• 119-36-8 methyl salicylate 
• 856306-04-2 2-propoxy-benzoic acid ethyl ester 
• 18167-33-4 methyl-2-propoxybenzoic acid 

Downstream Products

• 54090-36-7 2-propoxybenzoyl chloride 
• 503809-60-7 3-isobutyl-1-methyl-8-(2-propoxy-phenyl)-3,7-dihydro-purine-2,6-dione 
• 215299-78-8 5-Chlorosulphonyl-2-n-propoxybenzoic Acid 
• 139756-04-0 1-Methyl-4-(2-n-propoxybenzamido)-3-n-propylpyrazole-5-carboxamide 
• 130239-66-6 2-(2-propoxybenzamido)benzamide 
• 729594-53-0 2-propoxy-benzoic acid N'-(5-methyl-5H-1,2,4-triazino[5,6-b]indol-3-yl)-hydrazide 
• 18167-33-4 methyl-2-propoxybenzoic acid 
• 356044-98-9 1-methyl-3-(2-propoxybenzamido)-4-propyl-1H-pyrrole-2-carboxamide 
• 139756-23-3 5-(2-n-propoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one 
• 361340-57-0 1-methyl-5-(5-nitro-2-n-propoxyphenyl)-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one 
• 361340-58-1 5-(5-amino-2-n-propoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one 

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