3-Amino-2,3-dihydrobenzoic acid hydrochloride

Base Information

• Chemical Name: 3-Amino-2,3-dihydrobenzoic acid hydrochloride
• CAS No.: 59556-17-1
• Molecular Formula: C7H9 N O2 . Cl H
• Molecular Weight: 175.615
• Hs Code.: 2922499990
• European Community (EC) Number: 261-802-6
• UNII: C3VM79824Q
• DSSTox Substance ID: DTXSID10974965
• ChEMBL ID: CHEMBL1256019
• Mol file: 59556-17-1.mol

Synonyms:3-amino-2,3-dihydrobenzoic acid;gabaculin;gabaculine;gabaculine hydrochloride;gabaculine hydrochloride, (+-)-isomer;gabaculine, (+-)-isomer;gabaculine, (-)-isomer

Chemical Property of 3-Amino-2,3-dihydrobenzoic acid hydrochloride

Chemical Property:

• Vapor Pressure: 0.000198mmHg at 25°C
• Melting Point: 203 °C (dec.)(lit.)
• Boiling Point: 304.6°C at 760 mmHg
• Flash Point: 138°C
• PSA: 63.32000
• LogP: 1.78690
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 175.0400063
• Heavy Atom Count: 11
• Complexity: 206

Purity/Quality:

98%Min ^*data from raw suppliers

D,L-Gabaculine, Hydrochloride ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C=CC=C1C(=O)O)N.Cl
• Uses: 3-AMINO-2,3-DIHYDROBENZOIC ACID HYDROCHLORIDE is an irreversible inhibitor of mouse brain α-aminobutyric acid (GABA)-α-ketoglutarate transaminase. D,L-Gabaculine, Hydrochloride is an irreversible inhibitor of mouse brain α-aminobutyric acid (GABA)-α-ketoglutarate transaminase. An irreversible inhibitor of mouse brain a-aminobutyric acid (GABA)-a-ketoglutarate transaminase

Technology Process of 3-Amino-2,3-dihydrobenzoic acid hydrochloride

There total 8 articles about 3-Amino-2,3-dihydrobenzoic acid hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

5-(tert-butoxycarbonylamino)-1,3-cyclohexadienecarboxylic acid (59556-15-9) → gabaculin (59556-17-1)

Guidance literature:

In acetic acid;

DOI:10.1016/S0040-4039(00)99862-9

Reference yield:

1,2,5,6-tetrahydrobenzoic acid (4771-80-6) → gabaculin (59556-17-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 78.5 percent / ethylchloroformate, Et₃N, NaN₃

2: 50 percent / PPA / 0.17 h / 100 °C

3: SOCl₂ / methanol

4: Et₃N

5: 90 percent / Br₂, / CCl₄

6: 87 percent / LiBr, Li₂CO₃, / hexamethylphosphoric acid triamide / 1.) 20 deg C, 5 h, 2.) 40 deg C, 3.5 h

7: 89 percent / 2 percent NaOH / dioxane

8: 72 percent / acetic acid

With sodium hydroxide; thionyl chloride; sodium azide; bromine; chloroformic acid ethyl ester; lithium carbonate; triethylamine; lithium bromide; In 1,4-dioxane; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; acetic acid;

DOI:10.1016/S0040-4039(00)99862-9

Reference yield:

1-isocyano-3-cyclohexene (4103-88-2) → gabaculin (59556-17-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 50 percent / PPA / 0.17 h / 100 °C

2: SOCl₂ / methanol

3: Et₃N

4: 90 percent / Br₂, / CCl₄

5: 87 percent / LiBr, Li₂CO₃, / hexamethylphosphoric acid triamide / 1.) 20 deg C, 5 h, 2.) 40 deg C, 3.5 h

6: 89 percent / 2 percent NaOH / dioxane

7: 72 percent / acetic acid

With sodium hydroxide; thionyl chloride; bromine; lithium carbonate; triethylamine; lithium bromide; In 1,4-dioxane; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; acetic acid;

DOI:10.1016/S0040-4039(00)99862-9

upstream raw materials:

5-(tert-butoxycarbonylamino)-1,3-cyclohexadienecarboxylic acid

1,2,5,6-tetrahydrobenzoic acid

1-isocyano-3-cyclohexene

7-azabicyclo[3.2.1]oct-3-en-6-one