5-Norbornene-2-carboxylic acid
Uses- Product Name
- 5-Norbornene-2-carboxylic acid
- CAS No.
- 120-74-1
- Chemical Name
- 5-Norbornene-2-carboxylic acid
- Synonyms
- BICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXYLIC ACID;BICYCLO[2.2.1]-5-HEPTENE-2-CARBOXYLIC ACID;TIMTEC-BB SBB008175;5-Norbornene-2-carboxyL;Norbornenecarboxylic acid;5-Hyboratene-2-formic acid;5-Norbornene-2-carboxylicaci;5-NORBORNENE-2-CARBOXYLIC ACID;Norborn-2-ene-5-carboxylic acid;Norborn-5-ene-2-carboxylic acid
- CBNumber
- CB8421641
- Molecular Formula
- C8H10O2
- Formula Weight
- 138.16
- MOL File
- 120-74-1.mol
5-Norbornene-2-carboxylic acid Property
- Melting point:
- 32.5-35 °C
- Boiling point:
- 136-138 °C14 mm Hg(lit.)
- Density
- 1.129 g/mL at 25 °C(lit.)
- refractive index
- n20/D 1.494(lit.)
- Flash point:
- >230 °F
- storage temp.
- Sealed in dry,Room Temperature
- pka
- 4.63±0.20(Predicted)
- form
- Liquid or solid
- color
- Colorless to light yellow
- Odor
- at 100.00 %. fruity, green
- Odor Type
- fruity
- Water Solubility
- Not miscible with water.
- BRN
- 637167
- CAS DataBase Reference
- 120-74-1(CAS DataBase Reference)
- NIST Chemistry Reference
- Bicyclo(2.2.1)hept-5-ene-2-carboxylic acid(120-74-1)
- EPA Substance Registry System
- Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (120-74-1)
Safety
- Hazard Codes
- C
- Risk Statements
- 34
- Safety Statements
- 26-36/37/39-45-27
- RIDADR
- UN 3265 8/PG 3
- WGK Germany
- 3
- TSCA
- Yes
- HazardClass
- 8
- PackingGroup
- Ⅲ
- HS Code
- 29162090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H314Causes severe skin burns and eye damage
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P363Wash contaminated clothing before reuse.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- 446440
- Product name
- 5-Norbornene-2-carboxylic acid, mixture of endo and exo, predominantly endo
- Purity
- 98%
- Packaging
- 25ml
- Price
- $120
- Updated
- 2025/07/31
- Product number
- N0667
- Product name
- 5-Norbornene-2-carboxylic Acid
- Purity
- >98.0%(GC)(T)
- Packaging
- 5g
- Price
- $23
- Updated
- 2025/07/31
- Product number
- N0667
- Product name
- 5-Norbornene-2-carboxylic Acid
- Purity
- >98.0%(GC)(T)
- Packaging
- 25g
- Price
- $56
- Updated
- 2025/07/31
- Product number
- A601658
- Product name
- rac-(1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylicAcid
- Packaging
- 50mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- JK519194
- Product name
- 5-Norbornene-2-carboxylicacid,98%,mixtureofendoandexo,predominantlyendo
- Packaging
- 5g
- Price
- $21
- Updated
- 2021/12/16
5-Norbornene-2-carboxylic acid Chemical Properties,Usage,Production
Uses
rac-(1R,2R,4R)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid is a useful research chemical.
Chemical Properties
Colorless liquid
Uses
5-Norbornene-2-carboxylic acid is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.
Synthesis
6203-08-3
934-30-5
1. 0.510 mol (68.0 g) of anhydrous aluminum chloride was suspended in 660 mL of toluene. To the suspension was added 0.600 mol (51.7 g) methyl acrylate and stirred until the aluminum chloride was completely dissolved. 2. 0.600 mol (39.7 g) of newly cracked cyclopentadiene (dissolved in 340 mL of toluene) was added to the solution over 45 minutes. The reaction mixture was stirred at room temperature for 90 minutes and subsequently poured into water. 3. The toluene layer was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated to dryness under vacuum. Purification by vacuum distillation over a Vigreux column afforded methyl 5-norbornene-2-carboxylate in 66.3 g (74%) yield and 99% purity (GC). 4. 5-Norbornene-2-carboxylic acid was prepared by mixing 164 mmol (25.0 g) of methyl ester with 85 g of 10% NaOH solution at 60 °C until the ester layer disappeared. Cool the solution, wash with ether, and 235 mL of 1 M hydrochloric acid at 60-70 °C with stirring. 5. The acid layer was separated, dissolved in ethyl acetate, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated to dryness in vacuum to yield 18.2 g (80%). 1H and 13C NMR confirmed the product as 5-norbornene-2-carboxylic acid. 6. 132 mmol (18.2 g) of the acid was dissolved in 480 mL of dichloromethane and 2.66 mmol (0.205 mL) of N,N-dimethylformamide and 665 mmol (57.0 mL) of oxalyl chloride were added dropwise over 1 h. The reaction was purified by stirring for 1.5 h at room temperature. It was stirred at room temperature for 1.5 h. The solvent and excess oxalyl chloride were removed by evaporation under reduced pressure to give a brown oily residue in a yield of 18.1 g (88%). 7. 115 mmol (18.0 g) of chloroyl chloride was added to a mixture of diethylene glycol (57.5 mmol, 6.10 g) and pyridine (115 mmol, 9.09 g) and stirred at room temperature for 4 hours. 150 mL of dichloromethane and 100 mL of water were added and the organic layer was washed with water, sodium bicarbonate solution and hydrochloric acid solution and dried over anhydrous sodium sulfate. Filtered and concentrated to dryness to give a yellow oily residue in a yield of 18.9 g (95%). 1H and 13C NMR showed it to be predominantly a diester. 8. 54.5 mmol (18.9 g) of the diester was dissolved in 260 mL of dichloromethane. 15.3 mmol (2.08 g) of sodium acetate trihydrate was dissolved in a 39% peracetic acid solution of acetic acid (153 mmol, 29.8 g) and added dropwise to the diester solution over 30 minutes. The reaction mixture was stirred at room temperature for 4 h. The reaction mixture was washed with water and sodium bicarbonate solution. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give light yellow oily diethylene glycol di(5,6-epoxy-2-norbornanecarboxylate) in 19.8 g (96%) yield and 94% purity (GC).1H and 13C NMR confirmed the structure of the product.
References
[1] Patent: WO2005/89549, 2005, A1. Location in patent: Page/Page column 22-24
[2] Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 5, p. 175 - 184
[3] Tetrahedron, 1997, vol. 53, # 35, p. 11937 - 11952
5-Norbornene-2-carboxylic acid Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 5-Norbornene-2-carboxylic acid manufacturers
- Product
- 5-Norbornene-2-carboxylic acid 120-74-1
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 5tons
- Release date
- 2024-11-29
- Product
- 5-Norbornene-2-carboxylic acid 120-74-1
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 500000kg
- Release date
- 2022-11-15
- Product
- 5-Norbornene-2-carboxylic acid 120-74-1
- Price
- US $117.00-320.00/g
- Min. Order
- 25g
- Purity
- 0.97
- Supply Ability
- 10kg
- Release date
- 2023-10-25