3-(Methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Base Information

• Chemical Name: 3-(Methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• CAS No.: 36897-94-6
• Molecular Formula: C10H12 O4
• Molecular Weight: 196.2
• Hs Code.: 2918990090
• European Community (EC) Number: 225-494-7,676-688-7
• NSC Number: 168053,140603
• DSSTox Substance ID: DTXSID50885420
• Nikkaji Number: J208.809F
• Mol file: 36897-94-6.mol

Synonyms:36897-94-6;3-(Methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid;5-Norbornene-2,3-dicarboxylic Acid Monomethyl Ester;4883-79-8;3-methoxycarbonylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid;EINECS 225-494-7;NSC 168053;Norborene-2,3-dicarboxylic acid, monomethyl ester;Bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylic acid, 2-methyl ester;Bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylic acid, monomethyl ester;Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid, monomethyl ester;Methyl hydrogen (endo-endo)-bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylate;Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid, 2-methyl ester;Methyl hydrogen (endo-endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate;NSC168053;Monomethyl 5-Norbornene-2,3-dicarboxylate;Norborene-2, monomethyl ester;SCHEMBL960068;DTXSID50885420;3-(Methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylicacid;NSC140603;2-carbomethoxy-3-carboxy-5-norbornene;AKOS015917821;NSC 140603;NSC-140603;NSC-168053;AS-71173;CS-0332030;N0525;5-norbornene-2,3-dicarboxylic monomethyl ester;D78435;Methyl Hydrogen 5-Norbornene-2,3-dicarboxylate;Bicyclo[2.2.1]hept-5-ene-2, monomethyl ester;A874255;mono-methyl cis 5-norbornene-endo-2,3-dicarboxylate;mono-methyl cis-5-norbomene-endo-2,3-dicarboxylate;Norborn-5-ene-2,3-dicarboxylic acid 2-methyl ester;mono-methyl cis-5-norbornene-endo-2, 3-dicarboxylate;Bicyclo[2.2.1]hept-5-ene-2, monomethyl ester, (endo,endo)-;Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid, monomethyl ester, (endo,endo)-

Chemical Property of 3-(Methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Chemical Property:

• Melting Point: 100°C
• Boiling Point: 327.6°Cat760mmHg
• PKA: 4.19±0.40(Predicted)
• Flash Point: 130.4°C
• PSA: 63.60000
• Density: 1.322g/cm³
• LogP: 0.68230
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 196.07355886
• Heavy Atom Count: 14
• Complexity: 307

Purity/Quality:

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

NE ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1C2CC(C1C(=O)O)C=C2
• Uses: MonoMethyl 5-Norbornene-2,3-dicarboxylate is?a carboxylate derivative and can be used as a curing agent for epoxy resins.

Technology Process of 3-(Methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

There total 11 articles about 3-(Methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic 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: 95.0%

(1R,2R,3R,4S)-endo-3-(methoxycarbonyl)-bicyclo[2.2.1]hept-5-en-exo-2-carboxylic acid (R)-(+)-1-phenylethylamine salt → (1R,2R,3R,4S)-endo-3-(methoxycarbonyl)-bicyclo[2.2.1]hept-5-en-exo-2-carboxylic acid (4883-79-8,25925-29-5,36897-94-6,41527-42-8,96185-91-0,96243-73-1,96243-74-2,116404-46-7,123286-70-4,125226-91-7,131433-31-3,131433-32-4,142186-01-4,142186-02-5)

Guidance literature:

With hydrogenchloride; In water;

DOI:10.1002/chir.22404

Reference yield: 88.4%

dimethyl 5-cis-norbornene-2,3-dicarboxylate (3014-58-2,5826-73-3,7184-07-8,39589-98-5,116404-47-8,117604-28-1,135357-64-1) → bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid monomethyl ester (4883-79-8,25925-29-5,36897-94-6,41527-42-8,96185-91-0,96243-73-1,96243-74-2,116404-46-7,123286-70-4,125226-91-7,131433-31-3,131433-32-4,142186-01-4,142186-02-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 0 ℃; for 5h;

DOI:10.1016/j.tetlet.2003.09.131

Reference yield:

methanol (67-56-1) + (1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (2746-19-2) → bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid monomethyl ester (4883-79-8,25925-29-5,36897-94-6,41527-42-8,96185-91-0,96243-73-1,96243-74-2,116404-46-7,123286-70-4,125226-91-7,131433-31-3,131433-32-4,142186-01-4,142186-02-5)

Guidance literature:

Rate constant; Heating; and with 10percent H₂O;

upstream raw materials:

D,L-1-[N-(3-Methoxycarbonyl-5-norbornen-2-yl)carbamoyl]-5-fluorouracil

methanol

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

dimethyl 5-cis-norbornene-2,3-dicarboxylate

Downstream raw materials:

3-(methoxycarbonyl)bicyclo<2.2.1>heptane-2-carboxylic acid

methyl 6-(3-phenylpropylcarbamoyl)-bicyclo[2.2.1]hept-2-ene-1-carboxylate

Refernces

• 1、 Kovalenko, Vitaly N.,Kozyrkov, Yurii Yu.. "A simple method for resolution of endo-/exo-monoesters of trans-norborn-5-ene-2,3-dicarboxylic acids into their enantiomers". . p. 151 - 155. Retrieved 2015/03/04.
• 2、 Artem'eva,Kudryavtsev,Chupans,Denisov. "1H NMR study of esterification of norbornenedicarboxylic acid anhydride by lower aliphatic alcohols". . p. 440 - 442. Retrieved 2007/10/03.