2,2-Diaminoheptanedioic acid

Base Information

• Chemical Name: 2,2-Diaminoheptanedioic acid
• CAS No.: 2577-62-0
• Molecular Formula: C₇H₁₄N₂O₄
• Molecular Weight: 190.199
• DSSTox Substance ID: DTXSID70598484
• Nikkaji Number: J185.654E
• Wikidata: Q82494248
• Mol file: 2577-62-0.mol

Synonyms:2,2-diaminoheptanedioic acid;2577-62-0;(6R,2R)-DIAMINOPIMELIC ACID;SCHEMBL29290;DTXSID70598484;HAWJUUUDZFZUKG-UHFFFAOYSA-N;a,a inverted exclamation mark -Diaminopimelicacid;A818009

Chemical Property of 2,2-Diaminoheptanedioic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: ~295 °C (dec.)(lit.)
• Boiling Point: 426.7°Cat760mmHg
• PKA: 2.20±0.24(Predicted)
• Flash Point: 211.8°C
• PSA: 126.64000
• Density: 1.344g/cm³
• LogP: 0.38110
• XLogP3: -6.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 190.09535693
• Heavy Atom Count: 13
• Complexity: 203

Purity/Quality:

98%,99%, ^*data from raw suppliers

DL-2,6-Diaminopimelic acid ≥95% (TLC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCC(C(=O)O)(N)N)CC(=O)O
• Uses: DL-2,6-Diaminopimelic acid, a stereoisomer of meso-DAP, may be used as a reference material in assays used to identify markers of bacteria and fungi in the rumen of ruminants.

Technology Process of 2,2-Diaminoheptanedioic acid

There total 69 articles about 2,2-Diaminoheptanedioic acid 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: 98.0%

dimethyl (2R,6S)-2,6-bis[(tert-butoxycarbonyl)amino]heptanedioate (354576-23-1,370860-89-2) → (2R,6S)-2,6-diaminoheptanedioic acid (583-93-7,922-54-3,2577-62-0,14289-34-0,17121-19-6,1356383-43-1)

Guidance literature:

dimethyl (2R,6S)-2,6-bis[(tert-butoxycarbonyl)amino]heptanedioate; With hydrogenchloride; at 70 ℃; for 3h;

With methyloxirane; In ethanol; at 20 ℃; for 10h; Further stages.;

DOI:10.1021/jo010865a

Reference yield: 92.0%

(3R,7S)-[1,2]Diazepane-3,7-dicarboxylic acid (752179-45-6) → (2R,6S)-2,6-diaminoheptanedioic acid (583-93-7,922-54-3,2577-62-0,14289-34-0,17121-19-6,1356383-43-1)

Guidance literature:

With hydrogenchloride; hydrogen; platinum(IV) oxide; under 3040 Torr;

DOI:10.1248/cpb.43.535

Reference yield: 70.0%

5,5'-trimethylenedihydantoin (41980-32-9) → 2,6-diaminopimelic acid (922-54-3,2577-62-0,14289-34-0,17121-19-6,583-93-7,1356383-43-1)

Guidance literature:

With hydrogen bromide; for 36h; Heating;

upstream raw materials:

di-Z-meso-2,2'-diaminopimelic acid

L-2-amino-6-ketopimelate

(3R,7S)-[1,2]Diazepane-3,7-dicarboxylic acid

Succinimide

Downstream raw materials:

di-Z-meso-2,2'-diaminopimelic acid

rac-2,6-dibenzyloxycarbonylaminopimelic acid

meso-2,6-dibenzyloxycarbonylaminopimelic acid

(+/-)-trans-piperidine-2,6-dicarboxylic acid

Refernces

• 1、 Collier, Philip N.,Campbell, Andrew D.,Patel, Ian,Raynham, Tony M.,Taylor, Richard J. K.. "Enantiomerically pure α-amino acid synthesis via hydroboration - Suzuki cross-coupling". . p. 1802 - 1815. Retrieved 2007/10/03.
• 2、 Roberts, John L.,Chan, Cecil. "Asymmetric synthesis of differentially protected meso-2,6-diaminopimelic acid". . p. 7679 - 7682. Retrieved 2007/10/03.