693-57-2

Basic information

• Product Name: 12-AMINODODECANOIC ACID
• Synonyms: H-12-ADO-OH;NH2-(CH2)11-COOH;DODECANOICACID,12-AMINO-;12-Aminododecanic Acid;12-AMinododecanoic acid 95%;12-AminolauricAcid,98%;12-Ado-OH;12-Aminododecanoic acid≥ 99% (Titration)
• CAS NO: 693-57-2
• Molecular Formula: C₁₂H₂₅NO₂
• Molecular Weight: 215.33
• EINECS: 211-754-7
• Product Categories: omega-Aminocarboxylic Acids;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides
• Mol File: 693-57-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 185-187 °C(lit.)
• Boiling Point: 349.7 °C at 760 mmHg
• Flash Point: 280 °C
• Appearance: /
• Density: 0.957 g/cm³
• Vapor Pressure: 7.95E-06mmHg at 25°C
• Refractive Index: 1.469
• Storage Temp.: Store at 0°C
• Solubility: Aqueous Acid (Slightly), Aqueous Base (Slightly)
• PKA: pK1: 4.648(+1) (25°C)
• Water Solubility: 137mg/L at 20℃
• BRN: 907502
• CAS DataBase Reference: 12-AMINODODECANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 12-AMINODODECANOIC ACID(693-57-2)
• EPA Substance Registry System: 12-AMINODODECANOIC ACID(693-57-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 693-57-2(Hazardous Substances Data)

Usage

Description

12-Aminododecanoic acid is an alkane chain with terminal carboxlic acid and amine groups. The compound can be used as a PROTAC linker in the synthesis of PROTACs. The amino group (NH2) is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. The terminal carboxylic acid can react with primary amine groups of activated NHS ester to form a stable amide bond.

Chemical Properties

Light beige powder

Uses

12-Aminolauric Acid is an amino acid used as a reagent in organic synthesis of several compounds including phenylbutazone which is a new long-acting agent which displays improved pharmacokinectics based on human serum albumin as a drug carrier.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C12H25NO2/c13-11-9-7-5-3-1-2-4-6-8-10-12(14)15/h1-11,13H2,(H,14,15)

Synthetic route

2-azacyclotridecanone (947-04-6) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
With Acidovorax sp.T31 ω-laurolactam hydrolase; water In toluene at 35℃; for 17h; pH=7; aq. phosphate buffer; Enzymatic reaction;	99.7%
With hydrogenchloride
With potassium phosphate buffer In toluene at 30℃; for 2h; pH=7.0;	10 mmol
With whole cells or crude cell extract of recombinant E.coli BL21 (DE3) (pCom10_T31) In ethanol for 0.5h; pH=7.4; aq. buffer; Enzymatic reaction;	99 %Chromat.

12-nitrododecanoic acid (32571-74-7) → acetaldehyde (75-07-0) + 12-Aminododecanoic acid (693-57-2) + H2

Conditions	Yield
With ethanol; titanium(IV) oxide for 2.5h; Irradiation;	A n/a B 89% C n/a

12-oxododecanoic acid oxime (91694-67-6) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
With hydrogen; platinum(IV) oxide In methanol under 2280 Torr; for 1.5h;	87%

12-nitrododecanoic acid (32571-74-7) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
With ammonium formate; palladium on activated charcoal In methanol at 80℃; for 0.5h;	85%

1,12-Diaminododecane (2783-17-7) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
Pseudomonas K95	55%
Pseudomonas K95	49%

methyl 12-aminododecanoate (53005-24-6) → 2-azacyclotridecanone (947-04-6) + 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
With whole-cells or crude cell extract of recombinant E.coli BL21 (DE3) (pCom10_T31) In ethanol for 0.5h; pH=10; aq. buffer; Enzymatic reaction;	A 13% B n/a

12-aminododecanoic acid ethyl ester (53005-23-5) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
With hydrogenchloride

13-hydroxyimino-dotriacontanoic acid → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
With sulfuric acid und Erhitzen des Reaktionsprodukts mit konz. wss. HCl auf 180grad;

12-Acetamino-dodecansaeure-aethylester (693-37-8) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
With hydrogenchloride

ω-Amino-7-oxo-laurinsaeure (16595-67-8) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate

C36H60O30*C12H25NO2 → alpha cyclodextrin (10016-20-3) + 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
In water-d2 at 24.85℃; pH=7.3; Equilibrium constant; Decomposition;

2C36H60O30*C12H25NO2 → C36H60O30*C12H25NO2 + 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
In water-d2 at 24.85℃; pH=7.3; Equilibrium constant; Decomposition;

oxime of/the/ 12-oxo-eicosane-carboxylic acid-(1) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
With sulfuric acid anschliessend mit konz. Salzsaeure bei 180grad;

13-hydroxyimino-dotriacontanoic acid + sulfuric acid (7664-93-9) → 1-nonadecanamine (n-nonadecylamine) (14130-05-3) + Arachidic acid (506-30-9) + 12-Aminododecanoic acid (693-57-2) + Brassyloic acid

Conditions	Yield
Erhitzen des Rektionsprodukts mit konz. HCl auf 180grad;

12-oxododecanoic acid (3956-80-7) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.92 mg / hydroxylamine hydrochloride, aq. NaOH / ethanol / 0.17 h / 100 °C 2: 87 percent / H2 / PtO2 / methanol / 1.5 h / 2280 Torr View Scheme

cis-12,13-epoxystearic acid (32381-04-7, 32381-05-8, 38003-80-4, 61827-10-9) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 73 percent / HIO4 / H2O; 2-methyl-propan-2-ol / 5 h 2: 0.92 mg / hydroxylamine hydrochloride, aq. NaOH / ethanol / 0.17 h / 100 °C 3: 87 percent / H2 / PtO2 / methanol / 1.5 h / 2280 Torr View Scheme

(+/-)-cis-12,13-epoxy-9(Z)-octadecenoic acid (17966-13-1) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 93 percent / H2 / PtO2 / methanol / 0.75 h / 2280 Torr 2: 73 percent / HIO4 / H2O; 2-methyl-propan-2-ol / 5 h 3: 0.92 mg / hydroxylamine hydrochloride, aq. NaOH / ethanol / 0.17 h / 100 °C 4: 87 percent / H2 / PtO2 / methanol / 1.5 h / 2280 Torr View Scheme

7-[5-(acetylamino-methyl)-thiophen-2-yl]-heptanoic acid ethyl ester (738-84-1) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. HCl / Raney-Ni / methanol 2: aq. HCl View Scheme

2-(syn-2-Oxo-cyclohexyliden)-1-aza-cycloheptan (16595-61-2) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH / Heating 2: N2H4*H2O, KOH View Scheme

methyl 12-aminododecanoate (53005-24-6) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
With whole-cells of recombinant E.coli BL21 (DE3) (pCom10_T31) In ethanol pH=7.4; aq. buffer; Enzymatic reaction;

methyl n-dodecanoate (111-82-0) → 12-hydroxydodecanoic acid (505-95-3) + methyl 12-hydroxydodecanoate (71655-36-2) + 1,12-dodecanedioic acid (693-23-2) + 12-methoxy-12-oxododecanoic acid (3903-40-0) + methyl 12-aminododecanoate (53005-24-6) + 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
With NADH In aq. phosphate buffer Kinetics; Microbiological reaction;
Multi-step reaction with 2 steps 1: NADH / aq. phosphate buffer / Microbiological reaction 2: NADH / aq. phosphate buffer / Microbiological reaction View Scheme

methyl 11-formylundecanoate (2009-59-8) → 12-hydroxydodecanoic acid (505-95-3) + methyl 12-hydroxydodecanoate (71655-36-2) + 1,12-dodecanedioic acid (693-23-2) + 12-methoxy-12-oxododecanoic acid (3903-40-0) + methyl 12-aminododecanoate (53005-24-6) + 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
With NADH In aq. phosphate buffer Kinetics; Microbiological reaction;

12-hydroxydodecanoic acid (505-95-3) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
With L-alanin; sodium hydroxide In aq. buffer at 35℃; for 2h; pH=8 - 9.5; Enzymatic reaction;
With pyridoxal 5'-phosphate; MATITNHMPTAELQALDAAHHLHPFSANNALGEEGTRVITRARGVWLNDSEGEEILDAMAGLWCVNIGYGRDELAEVAARQMRELPYYNTFFKTTHVPAIALAQKLAELAPGDLNHVFFAGGGSEANDTNIRMVRTYWQNKGQPEKTVIISRKNAYHGSTVASSALGGMAGMHAQSGLIPDVHHINQPNWWAEGGDMDPEEFGLARARELEEAILELGENRVAAFIAEPVQGAGGVIVAPDSYWPEIQRICDKYDILLIADEVICGFGRTGNWFGTQTMGIRPHIMTIAKGLSSGYAPIGGSIVCDEVAHVIGKDEFNHGYTYSGHPVAAAVALENLRILEEENILDHVRNVAAPYLKEKWEALTDHPLVGEAKIVGMMASIALTPNKASRAKFASEPGTIGYICRERCFANNLIMRHVGDRMIISPPLVITPAEIDEMFVRIRKSLDEAQAEIEKQGLMKSA; MIKAYAALEANGKLQPFEYDPGALGANEVEIEVQYCGVCHSDLSMINNEWGISNYPLVPGHEVVGTVAAMGEGVNHVEVGDLVGLGWHSGYCMTCHSCLSGYHNLCATAESTIVGHYGGFGDRVRAKGVSVVKLPKGIDLASAGPLFCGGITVFSPMVELSLKPTAKVAVIGIGGLGHLAVQFLRAWGCEVTAFTSSARKQTEVLELGAHHILDSTNPEAIASAEGKFDYIISTVNLKLDWNLYISTLAPQGHFHFVGVVLEPLDLNLFPLLMGQRSVSASPVGSPATIATMLDFAVRHDIKPVVEQFSFDQINEAIAHLESGKAHYRVVLSHSKN; nicotinamide adenine dinucleotide phosphate; benzylamine In dimethyl sulfoxide at 37℃; for 24h; pH=8; Reagent/catalyst; pH-value; Solvent; Microbiological reaction; Enzymatic reaction;

cyclododecene (1501-82-2) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: ozone / 2.5 h / 5 °C / Molecular sieve 1.2: 0.5 h / 10 - 20 °C 2.1: ammonia; hydrogen / isopropyl alcohol / 60 °C / 36961.4 Torr View Scheme

12-oxododecanoic acid butyl ester → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
With ammonia; hydrogen In isopropyl alcohol at 60℃; under 36961.4 Torr;
With ammonia; hydrogen In isopropyl alcohol at 60℃; under 36961.4 Torr;

10-undecenoic acid (112-38-9) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen bromide / toluene / 1 h / 18 °C / Industrial scale 2: sodium carbonate / N,N-dimethyl acetamide / 1.5 h / 130 °C / Inert atmosphere 3: hydrogen / 0.67 h / 90 - 110 °C / 18751.9 Torr View Scheme

11-cyanoundecanoic acid (5810-18-4) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
With hydrogen at 90 - 110℃; under 18751.9 Torr; for 0.666667h; Temperature;
With ammonium hydroxide; Ru/SiC; hydrogen In propan-1-ol; water at 110℃; under 26252.6 Torr; for 1.5h; Autoclave;	9.7 g

methyl 12-hydroxydodecanoate (71655-36-2) → methyl 12-aminododecanoate (53005-24-6) + 12-Aminododecanoic acid (693-57-2)

Conditions

Yield

With pyridoxal 5'-phosphate; MATITNHMPTAELQALDAAHHLHPFSANNALGEEGTRVITRARGVWLNDSEGEEILDAMAGLWCVNIGYGRDELAEVAARQMRELPYYNTFFKTTHVPAIALAQKLAELAPGDLNHVFFAGGGSEANDTNIRMVRTYWQNKGQPEKTVIISRKNAYHGSTVASSALGGMAGMHAQSGLIPDVHHINQPNWWAEGGDMDPEEFGLARARELEEAILELGENRVAAFIAEPVQGAGGVIVAPDSYWPEIQRICDKYDILLIADEVICGFGRTGNWFGTQTMGIRPHIMTIAKGLSSGYAPIGGSIVCDEVAHVIGKDEFNHGYTYSGHPVAAAVALENLRILEEENILDHVRNVAAPYLKEKWEALTDHPLVGEAKIVGMMASIALTPNKASRAKFASEPGTIGYICRERCFANNLIMRHVGDRMIISPPLVITPAEIDEMFVRIRKSLDEAQAEIEKQGLMKSA; MIKAYAALEANGKLQPFEYDPGALGANEVEIEVQYCGVCHSDLSMINNEWGISNYPLVPGHEVVGTVAAMGEGVNHVEVGDLVGLGWHSGYCMTCHSCLSGYHNLCATAESTIVGHYGGFGDRVRAKGVSVVKLPKGIDLASAGPLFCGGITVFSPMVELSLKPTAKVAVIGIGGLGHLAVQFLRAWGCEVTAFTSSARKQTEVLELGAHHILDSTNPEAIASAEGKFDYIISTVNLKLDWNLYISTLAPQGHFHFVGVVLEPLDLNLFPLLMGQRSVSASPVGSPATIATMLDFAVRHDIKPVVEQFSFDQINEAIAHLESGKAHYRVVLSHSKN; nicotinamide adenine dinucleotide phosphate; benzylamine In dimethyl sulfoxide at 37℃; for 24h; pH=8; Microbiological reaction; Enzymatic reaction;

undec-10-enenitrile (53179-04-7) → 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: acetylacetonatodicarbonylrhodium(l); hydrogen; 1,2-bis-(diphenylphosphino)ethane / toluene / 2 h / 100 °C / 15001.5 Torr / Autoclave 2: oxygen / toluene / 24 h / 20 °C 3: hydrogen; Ru/SiC; ammonium hydroxide / propan-1-ol; water / 1.5 h / 110 °C / 26252.6 Torr / Autoclave View Scheme
Multi-step reaction with 3 steps 1: acetylacetonatodicarbonylrhodium(l); hydrogen; 6,6'-[[3,3',5,5'-tetrakis(1,1-dimethylethyl)-[1,1'-biphenyl]-2,2'-diyl]bis(oxy)]bis-dibenzo [d,f][1,3,2]-dioxaphosphepine / toluene / 24 h / 120 °C / 15001.5 Torr / Autoclave 2: oxygen / toluene / 24 h / 20 °C 3: hydrogen; Ru/SiC; ammonium hydroxide / propan-1-ol; water / 1.5 h / 110 °C / 26252.6 Torr / Autoclave View Scheme

1-adamantyl isocyanate (4411-25-0) + 12-Aminododecanoic acid (693-57-2) → 12-(3-adamantan-1-yl-ureido)dodecanoic acid (479413-70-2)

Conditions	Yield
In 1,2-dichloro-ethane for 6h; Heating;	100%
In chloroform for 10h; Heating / reflux;	100%
In hexane at 20℃;	39%
In chloroform	2.66 g (100%)
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane

di-tert-butyl dicarbonate (24424-99-5) + 12-Aminododecanoic acid (693-57-2) → N-(tert-butyloxycarbonyl)-12-aminododecanoic acid (18934-81-1)

Conditions	Yield
With triethylamine In dichloromethane	99%
With sodium hydroxide In water	97%
With triethylamine In methanol at 60℃; for 1h;	96%

methanol (67-56-1) + 12-Aminododecanoic acid (693-57-2) → 12-aminododecanoic acid methyl ester hydrochloride

Conditions	Yield
With hydrogenchloride at 50℃; for 4h;	99%
With thionyl chloride at 20℃; Reflux;	98%
With thionyl chloride at 0 - 20℃; for 9h; Inert atmosphere;	98%

triethylamine (121-44-8) + D-Glucono-1,5-lactone (90-80-2) + 12-Aminododecanoic acid (693-57-2) → 12-(D-gluconoylamino)dodecanoic acid triethylamine salt

Conditions	Yield
In methanol for 4h; Reflux;	99%

D-Glucono-1,5-lactone (90-80-2) + 12-Aminododecanoic acid (693-57-2) → C18H35NO8

Conditions	Yield
With triethylamine In methanol for 4h; Reflux;	99%

maleic anhydride (108-31-6) + 12-Aminododecanoic acid (693-57-2) → 12-(3-carboxyacryloylamino)dodecanoic acid (57079-17-1)

Conditions	Yield
With lutidine In diethylene glycol dimethyl ether	98%
With acetic acid Ambient temperature;	85%
In acetic acid

phthalic anhydride (85-44-9) + 12-Aminododecanoic acid (693-57-2) → 12-(1,3-dioxoisoindolin-2-yl)dodecanoic acid (21084-58-2)

Conditions	Yield
With triethylamine In toluene for 1.5h; Heating;	98%
With triethylamine In toluene for 12h; Heating;	80%
In toluene Heating;	36%
at 150℃; for 0.75h; Yield given;

12-Aminododecanoic acid (693-57-2) → methyl 12-aminododecanoate (53005-24-6)

Conditions	Yield
With hydrogenchloride; sodium hydrogencarbonate In methanol; water	98%
With sulfuric acid; sodium carbonate In methanol	95%
With sulfuric acid In methanol for 24h; Reflux;	70%

trifluoroacetic acid-methyl ester (431-47-0) + 12-Aminododecanoic acid (693-57-2) → 12-(2,2,2-trifluoroacetamido)dodecanoic acid (124051-56-5)

Conditions	Yield
With triethylamine In methanol for 18h;	97%
With triethylamine In methanol at 20℃; for 18h;	92%

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) + 12-Aminododecanoic acid (693-57-2) → N,N’-di(1-carboxylundecyl)-3,4,9,10-perylenetetracarboxyldiimide (118902-46-8)

Conditions	Yield
With 1H-imidazole at 120℃; for 1h; Schlenk technique; Inert atmosphere;	96%
In 1-methyl-pyrrolidin-2-one
In 1-methyl-pyrrolidin-2-one at 110℃; for 24h; Inert atmosphere;

Methacryloyl chloride (920-46-7) + 12-Aminododecanoic acid (693-57-2) → 12-(methacrylolamino)dodecanoic acid (62839-65-0)

Conditions	Yield
With sodium hydrogencarbonate; 4-methoxy-phenol In acetone for 1h; Heating;	95%
In 1,4-dioxane; water	73%
Stage #1: 12-Aminododecanoic acid With sodium hydroxide In water for 0.5h; Stage #2: Methacryloyl chloride In water at -5 - 0℃; for 1.25h; Stage #3: With hydrogenchloride In water pH=<= 3;

ethanol (64-17-5) + 12-Aminododecanoic acid (693-57-2) → 12-aminododecanoic acid ethyl ester (53005-23-5)

Conditions	Yield
Stage #1: ethanol With acetyl chloride at 20℃; for 1h; Stage #2: 12-Aminododecanoic acid at 20℃; for 0.25h;	94%
With sulfuric acid Reflux;

ethanol (64-17-5) + 12-Aminododecanoic acid (693-57-2) → ethyl 12-aminododecanoate hydrochloride (84636-23-7)

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 12h;	93%
With thionyl chloride at 0 - 20℃; for 2.33333h;

5-(dimethylamino)naphth-1-ylsulfonyl chloride (605-65-2) + 12-Aminododecanoic acid (693-57-2) → 12-N-(5'-dimethylaminonaphthalene-1'-sulfonyl)aminododecanoic acid

Conditions	Yield
With sodium hydrogencarbonate; triethylamine In acetone at 20℃; for 1h;	92%
With sodium hydrogencarbonate In water; acetone at 20℃; for 5h;	60%

succinimidyl 4-azido-2,3,5,6-tetrafluorobenzoate (126695-58-7) + 12-Aminododecanoic acid (693-57-2) → 12-[N-(4-azido-2,3,5,6-tetrafluorobenzoyl)]amidododecanoic acid (254968-74-6)

Conditions	Yield
In 1,4-dioxane at 50 - 60℃; for 4h;	90%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 12-Aminododecanoic acid (693-57-2) → 9-fluorenylmethoxycarbonyl-12-aminododecanoic acid (128917-74-8)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water	90%
With sodium carbonate In 1,4-dioxane at 0 - 20℃;	78.3%
With sodium carbonate In 1,4-dioxane; water at 0 - 20℃;

sulfuric acid (7664-93-9) + dihydrogen peroxide (7722-84-1) + 12-Aminododecanoic acid (693-57-2) → 12-aminoperlauric acid monopersulfate

Conditions	Yield
In ethyl acetate	90%

4-chloro-2H-1-benzopyran-2-one (17831-88-8) + 12-Aminododecanoic acid (693-57-2) → 12-((2-oxo-2H-chromen-4-yl)amino)dodecanoic acid

Conditions	Yield
With copper(l) iodide; potassium carbonate In water at 80℃; Ullmann Condensation; Microwave irradiation;	90%

2,2,2-trichloro-1,1-dimethylethoxychloroformate (66270-36-8) + 12-Aminododecanoic acid (693-57-2) → 12-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-dodecanoic acid (250142-13-3)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane at 20℃; for 0.166667h; Acylation;	88.7%

C37H44N3O4(1+)*Br(1-) + 12-Aminododecanoic acid (693-57-2) → C45H64N3O3(1+)*Br(1-)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	88%

pyridine-2-carbaldehyde (1121-60-4) + 12-Aminododecanoic acid (693-57-2) → sodium 12-{[(pyridin-2-yl)methylene]amino}undecanoate

Conditions	Yield
Stage #1: 12-Aminododecanoic acid With sodium hydroxide In methanol Stage #2: pyridine-2-carbaldehyde In methanol at 20℃; for 12h;	87%

diisopropyl hydrogenphosphonate (1809-20-7) + 12-Aminododecanoic acid (693-57-2) → 12-(diisopropoxy-phosphorylamino)-dodecanoic acid (869337-31-5)

Conditions	Yield
With triethylamine In tetrachloromethane; ethanol; water at 0 - 20℃;	87%

NBD chloride (10199-89-0) + 12-Aminododecanoic acid (693-57-2) → 12-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)dodecanoic acid (96801-39-7)

Conditions	Yield
With sodium hydrogencarbonate In water; acetonitrile at 65℃; for 2h;	87%
With sodium hydrogencarbonate In methanol at 0 - 50℃; for 3.5h;	81%
With sodium hydrogencarbonate In methanol; water at 50℃; for 1.5h;	64%
Stage #1: 12-Aminododecanoic acid With sodium hydrogencarbonate In ethanol; water at 37℃; for 0.166667h; Inert atmosphere; Stage #2: NBD chloride In ethanol; water at 37℃; Inert atmosphere;	56%
With sodium hydrogencarbonate In methanol at 50℃; for 3h;	36%

12-Aminododecanoic acid (693-57-2) + 1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride (156028-26-1) → C48H50Cl4N2O8

Conditions	Yield
With propionic acid at 140℃; for 36h; Inert atmosphere; Schlenk technique;	87%
In 1-methyl-pyrrolidin-2-one at 20 - 65℃; for 1.5h;

benzoic acid anhydride (93-97-0) + 12-Aminododecanoic acid (693-57-2) → 12-(benzoylamino)dodecanoic acid

Conditions	Yield
With acetic acid at 20℃; for 2.5h;	86%

methanol (67-56-1) + 12-Aminododecanoic acid (693-57-2) → methyl 12-aminododecanoate (53005-24-6)

Conditions	Yield
With thionyl chloride at -10 - 20℃;	86%
With thionyl chloride
With acetyl chloride at 0℃; for 3h; Inert atmosphere; Reflux;

2,4-Dinitrofluorobenzene (70-34-8) + 12-Aminododecanoic acid (693-57-2) → N-(2,4-dinitrophenyl)-12-aminododecanoic acid

Conditions	Yield
Stage #1: 12-Aminododecanoic acid With potassium hydroxide In 1,4-dioxane for 0.0833333h; Stage #2: 2,4-Dinitrofluorobenzene In 1,4-dioxane for 18h;	86%

Upstream product

• 32571-74-7 12-nitrododecanoic acid 
• 111-82-0 methyl n-dodecanoate 
• 2009-59-8 methyl 11-formylundecanoate 
• 2783-17-7 1,12-Diaminododecane 
• 16595-67-8 ω-Amino-7-oxo-laurinsaeure 
• 693-37-8 12-Acetamino-dodecansaeure-aethylester 
• 53005-23-5 12-aminododecanoic acid ethyl ester 
• 13050-14-1 12-oxododecanenitrile 
• 53179-04-7 undec-10-enenitrile 
• 71655-36-2 methyl 12-hydroxydodecanoate 
• 5810-18-4 11-cyanoundecanoic acid 
• 112-38-9 10-undecenoic acid 
• 1501-82-2 cyclododecene 
• 505-95-3 12-hydroxydodecanoic acid 

Downstream Products

• 1438405-23-2 C₃₈H₄₇NO₂P₂ 
• 14502-45-5 12-bromododecylamine hydrobromide 

Relevant articles and documents

The screening, characterization, and use of ω-laurolactam hydrolase: A new enzymatic synthesis of 12-aminolauric acid

Several ω-laurolactam degrading microorganisms were isolated from soil samples. These strains were capable of growing in a medium containing ω-laurolactam as sole source of carbon and nitrogen. Among them, five strains (T7, T31, U124, U224, and U238) were identified as Cupriavidus sp. T7, Acidovorax sp. T31, Cupriavidus sp. U124, Rhodococcus sp. U224, and Sphingomonas sp. U238, respectively. The ω-laurolactam hydrolyzing enzyme from Rhodococcus sp. U224 was purified to homogeneity, and its enzymatic properties were characterized. The enzyme acts on ω-octalactam and ω-laurolactam, but other lactam compounds, amides and amino acid amides, cannot be substrates. The enzyme gene was cloned, and the deduced amino acid sequence showed high homology with 6-aminohexanoate-cyclic-dimer hydrolase (EC 3.5.2.12) from Arthrobacter sp. KI72 and Pseudomonas sp. NK87. Enzymatic synthesis of 12-aminolauric acid was performed using partially purified ω-laurolactam hydrolase from Rhodococcus sp. U224.

Amino acid preparation method comprising a step of hydroformylation of an unsaturated fatty nitrile

A process for synthesizing an ω-amino acid compound of formula [in-line-formulae]HOOC—(CH2)r+2—CH2NH2,[/in-line-formulae] wherein 4≤r≤13 from a monounsaturated fatty nitrile compound of formula [in-line-formulae]CH2═CH—(CH2)r—CN[/in-line-formulae] the process comprising: 1) a step of hydroformylation of the mono unsaturated fatty nitrile compound by reacting said nitrile with carbon monoxide and di hydrogen 5e-a5 to obtain a nitrile aldehyde compound of formula HOC—(CH2)r+2-CN, then 2) a step of oxidation, in the presence of dioxygen, of the nitrile aldehyde compound to obtain a corresponding nitrile acid compound of formula HOOC—(CH2)r+2-CN, and 3) a step of reduction of the nitrile acid compound to give an w-amino acid of formula [in-line-formulae]HOOC—(CH2)r+2—CH2NH2.[/in-line-formulae]

Method for preparing 12-aminododecanoic acid

The invention relates to a method for preparing 12-aminododecanoic acid and belongs to the technical field of synthesis of long carbon chain nylon monomers. The method comprises the following steps: carrying out a substitution reaction on 10-undecenoic acid and hydrogen bromide to produce 11-bromo-undecanoic acid; carrying out a hydrocyanation reaction with a cyanide reagent K[Fe(CN)6].3H2O to produce 11-cyan-undecanoic acid; and carrying out a reduction reaction, thereby obtaining the final product 12-aminododecanoic acid. The method disclosed by the invention has the advantages of being short in synthetic route, low in cost, flexible in operation, high in reaction yield, capable of obtaining the high-purity product and the like, and is very suitable for small-dose large-scale production of pharmaceutical companies or labs.